Functional_group

In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction(s) regardless of the size of the molecule it is a part of.
Combining the names of functional groups with the names of the parent alkanes generates a powerful systematic nomenclature for naming organic compounds.

Contents

1 Table of common functional groups
2 See also
3 References
4 External links
5 Credits



The non-hydrogen atoms of functional groups are always associated with each other and with the rest of the molecule by covalent bonds. When the group of atoms is associated with the rest of the molecule primarily by ionic forces, the group is referred to more properly as a polyatomic ion or complex ion—all of these are called radicals, by a meaning of the term radical that predates the free radical.
The first carbon atom after the carbon that attaches to the functional group is called the alpha carbon.
Functional groups are attached to the carbon backbone of organic molecules. They determine the characteristics and chemical reactivity of molecules. Functional groups are far less stable than the carbon backbone and are likely to participate in chemical reactions.

Table of common functional groups
The following is a list of common functional groups. In the formulas, the symbols R and R' usually denotes an attached hydrogen, or a hydrocarbon side chain of any length, but may sometimes refer to any group of atoms. Below is an image of multiple functional groups found in organic chemistry.
(For convenience, see basic functional groups covered in General Biology)



Chemical class

Group

Formula

Structural Formula

Prefix

Suffix

Example


Acyl halide
Haloformyl

RCOX



haloformyl-
-oyl halide


Acetyl chloride
(Ethanoyl chloride)


Alcohol
Hydroxyl

ROH



hydroxy-
-ol


Methanol


Aldehyde
Aldehyde

RCHO



aldo-
-al


Acetaldehyde
(Ethanal)


Alkane
Alkyl

RH



alkyl-
-ane


Methane


Alkene
Alkenyl

R2C=CR2



alkenyl-
-ene


Ethylene
(Ethene)


Alkyne
Alkynyl

RC≡CR'



alkynyl-
-yne


Amide
Carboxamide

RCONR2



carboxamido-
-amide


Amines

Primary amine

RNH2



amino-
-amine


Methylamine
(Methanamine)


Secondary amine

R2NH



amino-
-amine


Dimethylamine


Tertiary amine

R3N



amino-
-amine


Trimethylamine


4° ammonium ion

R4N+



ammonio-
-ammonium


Choline


Azide

Azide

RN3



azido-
alkyl azide


Phenyl azide
(Azidobenzene)


Azo compound

Azo
(Diimide)

RN2R'



azo-
-diazene


Methyl orange
(p-dimethylamino-azobenzenesulfonic acid)


Toluene derivative

Benzyl

RCH2C6H5
RBn



benzyl-

1-(substituent)toluene


Benzyl bromide
(1-Bromotoluene)


Carbonate

Carbonate ester

ROCOOR





alkyl carbonate




Carboxylate

Carboxylate
RCOO−






carboxy-
-oate


Sodium acetate
(Sodium ethanoate)


Carboxylic acid

Carboxyl
RCOOH



carboxy-
-oic acid


Cyanates

Cyanate
ROCN



cyanato-

alkyl cyanate




Thiocyanate
RSCN



thiocyanato-

alkyl thiocyanate




Disulfide
Disulfide

RSSR'





alkyl alkyl disulfide

File:Cystamine.svg
Cystamine
(2,2'-Dithiobis(ethylamine))


Ether
Ether

ROR'



alkoxy-

alkyl alkyl ether


Diethyl ether
(Ethoxyethane)


Ester
Ester

RCOOR'




alkyl alkanoate


Ethyl butyrate
(Ethyl butanoate)


Haloalkane
Halo

RX



halo-
alkyl halide


Chloroethane
(Ethyl chloride)


Hydroperoxide

Hydroperoxy

ROOH



hydroperoxy-

alkyl hydroperoxide


Methyl ethyl ketone peroxide


Imine

Primary ketimine

RC(=NH)R'



imino-
-imine




Secondary ketimine

RC(=NR)R'



imino-
-imine




Primary aldimine

RC(=NH)H



imino-
-imine




Secondary aldimine

RC(=NR')H



imino-
-imine




Imide
Imide

RC(=O)NC(=O)R'



imido-

-imide


Isocyanide
Isocyanide

RNC



isocyano-

alkyl isocyanide




Isocyanates

Isocyanate
RNCO



isocyanato-

alkyl isocyanate


Methyl isocyanate


Isothiocyanate
RNCS



isothiocyanato-

alkyl isothiocyanate


Allyl isothiocyanate


Ketone
Carbonyl

RCOR'



keto-, oxo-
-one


Methyl ethyl ketone
(Butanone)


Nitrate
Nitrate

RONO2



nitrooxy-, nitroxy-

alkyl nitrate



Amyl nitrate
(1-nitrooxypentane)


Nitrile
Nitrile

RCN



cyano-

alkanenitrile

alkyl cyanide



Benzonitrile
(Phenyl cyanide)


Nitrite
Nitrosooxy

RONO



nitrosooxy-

alkyl nitrite



Amyl nitrite
(3-methyl-1-nitrosooxybutane)


Nitro compound

Nitro

RNO2



nitro-
 


Nitromethane


Nitroso compound

Nitroso
RNO



nitroso-
 


Nitrosobenzene


Peroxide

Peroxy

ROOR



peroxy-

alkyl peroxide


Di-tert-butyl peroxide


Benzene derivative

Phenyl

RC6H5



phenyl-
-benzene


Cumene
(2-phenylpropane)


Phosphine
Phosphino

R3P



phosphino-
-phosphane


Methylpropylphosphane


Phosphodiester

Phosphate

HOPO(OR)2



phosphoric acid di(substituent) ester

di(substituent) hydrogenphosphate

DNA


Phosphonic acid
Phosphono

RP(=O)(OH)2



phosphono-

substituent phosphonic acid


Benzylphosphonic acid


Phosphate
Phosphate

ROP(=O)(OH)2



phospho-



Glyceraldehyde 3-phosphate


Pyridine derivative

Pyridyl

RC5H4N











4-pyridyl
(pyridin-4-yl)


3-pyridyl
(pyridin-3-yl)


2-pyridyl
(pyridin-2-yl)


-pyridine


Nicotine


Sulfide



RSR'





di(substituent) sulfide


Dimethyl sulfide


Sulfone

Sulfonyl

RSO2R'



sulfonyl-

di(substituent) sulfone


Dimethyl sulfone
(Methylsulfonylmethane)


Sulfonic acid
Sulfo

RSO3H



sulfo-

substituent sulfonic acid


Benzenesulfonic acid


Sulfoxide

Sulfinyl

RSOR'



sulfinyl-

di(substituent) sulfoxide


Diphenyl sulfoxide


Thiol

Sulfhydryl

RSH



mercapto-, sulfanyl-

-thiol


Ethanethiol
(Ethyl mercaptan)

See also
Chemical classification
Organic chemistry
ReferencesISBN links support NWE through referral fees
McMurry, John. Organic Chemistry. 6th ed. Belmont, CA: Brooks/Cole, 2004. ISBN 0534420052
Morrison, Robert T., and Robert N. Boyd. Organic Chemistry. 6th ed. Englewood Cliffs, NJ: Prentice Hall, 1992. ISBN 0-13-643669-2
Solomons, T.W. Graham, and Fryhle, Craig B. Organic Chemistry. 8th ed. Hoboken, NJ: John Wiley, 2004. ISBN 0471417998
External links
All links retrieved May 16, 2017.

IUPAC Compendium of Chemical Terminology - the Gold Book International Union of Pure and Applied Chemistry.




Functional groups


Chemical class: Alcohol • Aldehyde • Alkane • Alkene • Alkyne • Amide • Amine • Azo compound • Benzene derivative • Carboxylic acid • Cyanate • Ester • Ether • Haloalkane • Imine • Isocyanide • Isocyanate • Ketone • Nitrile • Nitro compound • Nitroso compound • Peroxide • Phosphoric acid • Pyridine derivative • Sulfone • Sulfonic acid • Sulfoxide • Thioether • Thiol • Toluene derivative



Topics in organic chemistry



Aromaticity | Covalent bonding | Functional groups | Nomenclature | Organic compounds | Organic reactions | Organic synthesis | Publications | Spectroscopy | Stereochemistry



List of organic compounds


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